Butyric anhydride → N-[4-(methoxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylbutanamide ethanedioate

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5]1.[C:25]([O:30][C:31](=[O:35])[CH2:32]CC)(=[O:29])[CH2:26][CH2:27][CH3:28].[OH-:36].[NH4+]>>[C:31]([OH:30])(=[O:35])[C:32]([OH:2])=[O:36].[CH3:1][O:2][CH2:3][C:4]1([N:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:25](=[O:29])[CH2:26][CH2:27][CH3:28])[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:6][CH2:5]1

Participants

Reactant 3

HCID 7798Butyric anhydride

HCID 14923Ammonium Hydroxide

HCID 122982104-Piperidinamine, 4-(methoxymethyl)-N-phenyl-1-(2-phenylethyl)-

Product 1

HCID 12298012N-[4-(methoxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylbutanamide ethanedioate

Procedure

A mixture of 3 parts of 4-(methoxymethyl)-N-phenyl-1-(2-phenylethyl)-4-piperidinamine and 5 parts of butanoic acid, anhydride is stirred and refluxed for 8 hours. The reaction mixture is poured onto water and the whole is alkalized with ammonium hydroxide. The product is extracted with trichloromethane. The extract is washed with water, dried, filtered and evaporated. The oily residue is stirred in 1,1'-oxybisethane with activated charcoal. The latter is filtered off and the filtrate is evaporated. The residue is converted into the ethanedioate salt 2-propanol. The salt is filtered off and crystallized from 2-propanone, yielding 1.7 parts of N-[4-(methoxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylbutanamide ethanedioate; mp. 174.2° C.